Dioxygen-induced oxidative activation of a P-H bond: radical oxyphosphorylation of alkenes and alkynes toward β-oxy phosphonates

Pan Peng; Qingquan Lu; Long Peng; Chao Liu; Guangyu Wang; Aiwen Lei

doi:10.1039/c6cc06881b

Dioxygen-induced oxidative activation of a P-H bond: radical oxyphosphorylation of alkenes and alkynes toward β-oxy phosphonates

Chem Commun (Camb). 2016 Oct 11;52(83):12338-12341. doi: 10.1039/c6cc06881b.

Authors

Pan Peng¹, Qingquan Lu¹, Long Peng¹, Chao Liu¹, Guangyu Wang¹, Aiwen Lei²

Affiliations

¹ College of Chemistry and Molecular Sciences, The Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, Hubei, P. R. China. aiwenlei@whu.edu.cn.
² College of Chemistry and Molecular Sciences, The Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, Hubei, P. R. China. aiwenlei@whu.edu.cn and National Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang, 330022, P. R. China.

PMID: 27711459
DOI: 10.1039/c6cc06881b

Abstract

The dioxygen-induced radical oxyphosphorylation of alkenes and alkynes is presented, wherein a P-H bond was activated by molecular oxygen. Various β-oxy phosphonates could be facilely synthesized without the assistance of any transition metals or extra organic initiators. Mechanistic studies showed that HP(O)Ph₂ acts as a reductant to accelerate oxyphosphorylation.